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The 50 Greatest Streetwear T-Shirts of All Time

If anyone were to ever take on the daunting task of thoroughly documenting all the players and personalities that have enabled the world of streetwear to prosper in just a few decades, certain names would require a lot more ink than others. James Jebbia, Eric Brunetti, Bobby Hundreds, Nigo, and so many others have been instrumental in creating a global industry that has adapted to and thrived within changes in political climate, advances in technology, and survived all manner of fleeting trends. Another name that deserves authoritative status and multiple pages when telling the story of streetwear: Jeff Staple.

Jeff's knowledge of streetwear's past and present, and his participation in molding its future all afford him the title of expert, and when it comes to a Herculean task like cobbling together the 50 greatest streetwear T-shirts of all time, he's one of the few dudes who can be trusted to execute.

At his own admission, ranking from the fiftieth best to number one would be an impossible task. Instead, he chose 50 tees that either represent strokes of genius design, conveyed powerful messages that went beyond streetwear, and pieces that set new benchmarks for the entire game. Roughly chronologically ordered, the T-shirts he chose cover four distinct eras in streetwear's existence: Streetwear B.C.; The Wonder Years; The Streetwear Explosion; and Streetwear 2Day. Any historian will note that these distinctive periods do bleed into one another in terms of time, but the beauty is that these trace the ongoing evolution of streetwear, a genre that always blurred lines and never stuck to set definitions imposed by others.

You may have owned a few of these T-shirts. Others, you may be seeing for the first time. But with each one, Jeff Staple gave the reasoning why it's deserving to be called one of the greatest ever. Each one of them has a story, and each one was an integral part in the evolution of streetwear, and the legacy that it leaves in influencing future creations. These are The 50 Greatest Streetwear T-Shirts of All Time, as Told by Jeff Staple.